Startup Diary: Entry 4. I think I’m gonna need a bigger boat.

About two months ago, the thought hit me like a frying pan over the head: I needed a partner to help me build and run my school for startups. At the time, I was managing six freelancers, each in a different state. I was bootstrapping, so I had taken a pass on the expensive project managers, and I was running everything myself.

But tasks were slipping through the cracks. There were just too many details, many of which were outside of my primary areas of expertise. What I needed was a Mr. / Mrs. Inside to my Mr. Outside. Someone to run product development and operations. Someone who had done it before, and done it well.

Deciding you need a partner is of course only part of the challenge. Next you have to find someone with the right stuff, make sure you are a good fit, negotiate a deal, and learn to work together well. Over the next few posts, I’ll explore each of those issues.

Got any tips or stories about partnering? Please chime in.

Startup Diary: Entry 3 (hair on fire)

If I had hair, it would be on fire today. I’m only a few days into my startup, but there’s already so much to do, it’s nearly overwhelming (It’s also exhilarating, and I’m a closet stressmonger. Shhhh).

As an entrepreneur, with or without hair, you’ve got to wear a lot of hats. Today, I drafted the content for an online class, hired a graphic artist to design my book cover, pitched my business to a potential marketing partner, made some changes to my legal entity with my lawyer, and conducted a client coaching session.

But the toughest part about a day in the life as an entrepreneur is the tyranny of choice. There are 100+ things on my to-do list, and nobody to tell me what’s what. So, I’ve got to prioritize up the wazoo. That’s one of the untold secrets of entrepreneurial success: Figure out what to do now, and what NOT to do now (aka ever).

Startup Diary: Entry 2

When I meet with a client planning a business, the first question I ask is “what are your goals?” So simple, but it’s amazing how many people get started before they think through their goals. Setting goals gives you a sense for whether all the hard work could payoff in a way that makes it worthwhile to you. Goals also frame the way you’ll approach raising capital (e.g. if you are looking to build a modest sized business, rule out venture capital). And of course, without goals, it’s tough to measure your performance.

Here are my goals:

• Keep startup costs below $25,000 for the first 3 months of operations, and again for the second 3 months (if I get there). I’m bootstrapping this. In part to practice what I preach – stay lean, move fast, and take a phased approach to maximize flexibility and reduce risk. I’m also bootstrapping out of necessity. I have a new baby at home, got burned by Madoff, and have most of my assets tied up in illiquid investments. Not ideal, but it sure does light a fire under my behind. I won’t rule out raising capital in some way or another down the road, but first I want to get some traction and understand the dynamics of the business.
• Generate revenue within 3 months, and reach break-even within 6 months. This goes hand in hand with bootstrapping. I don’t want to empty my savings account into this venture. Starting TODAY, the meter is running.
• Build a business that can generate over $1MM in revenue / yr, profitably, within 3 years. I’d like the company to throw off enough cash so I can support my family and save for the future (btw I live in NYC so that’s a lot).
• Maximize the chances of success.  I’ve tried swinging for the $100MM fences, and it’s a rush. But right now I’d rather have a 90% chance of building a business with modest revenue and profits, than a 2% chance of hitting it big.
• Create assets I could potentially sell down the road. That means I need an exit strategy – a sense for what this could be worth, to whom, and when.
• Work with a small team of people I like and relate to, within a flat organization. I don’t want to spend my time managing a big team. I’d rather have a few key lieutenants or partners.

Did I leave anything out? Screw anything up? What do you think?

Startup Diary: Entry 1

I write a blog about planning and launching businesses. And now I’m planning to launch a new business myself. So, it just seems natural to share my experiences in the blog.

First, a little background.  After a few years of jobs with bosses and paychecks, I set out to become an entrepreneur. My first startup was a social network based on alumni affiliations, launched in 1996 (too early; my bad).  My second startup ran ads and promotions on milk containers. Odd, but it worked out well, despite my lactose intolerance.

In between launching ventures, I did consulting for other startups. I helped Moby, the musician, launch an iced-tea business. I helped the world’s top makeup artist plan a cosmetics business. I worked with Mark Gordon, a big Hollywood producer (Gray’s Anatomy, 2012, Saving Private Ryan), assessing some innovative startup ideas. And I helped athlete and journalist Tiki Barber with some of his sports and philanthropic ventures.

That all worked out well, but I needed to build something.  Also, most entrepreneurs can’t afford consultants, so I wanted to teach them how to plan and launch companies themselves.

That brings me to today. It’s just after New Year’s, 2010. And I’m planning to build an online school for startups.  As I develop my business plan and launch the business, I’ll keep you posted. I’ll be open with you about what’s working and what’s not, and about both the hard facts and the underlying emotions. Along the way, please post comments about anything that comes to mind. It’s too hard and lonely to go this alone – I need your help.